Answers

What is the kind of product key you used? Was the machine activated by KMS host? If so, you may need to install the KMS Client setup key to switch the
product back to KMS client. The KMS Client setup key for Windows Server 2008 R2 Enterprise is: 489J6-VHDMP-X63PK-3K798-CPX3Y

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After the DISM upgrade I switched back to my original MAK key (and activated successfully). A secondary behavior of this was that Remote Desktop was no longer functional on any machine that used the MAK Key. I then did some additional research
and found that other people had experienced the same problem using the DISM upgrade (http://social.technet.microsoft.com/Forums/en-US/winserverTS/thread/6debc586-0977-4731-b418-ca1edb34fe8b).
On a hunch I switched back to the KMS key and was then able to install SP1 (and remote desktop was reenabled). I then tried a Std/Enterprise license from a different MSDN account and it activated successfully, as well as kept Remote Desktop enabled.
I also tested switching back to my original MAK key and this worked as well. I then just switched the rest of my VM's to the new MSDN key and this was successful as well, without re-introducing the KMS key.

Best I can tell, there must be something unique to using the same key at each end of the standard -> enterprise DISM upgrade path path. I've got my environment back up and running and all at SP1 but I can fire up a test VM to test a different scenario.

All replies

Is the VM a DC? As I know, the server can’t be a DC at the time of upgrade.

It seems that the In-place upgrade doesn’t work completely. There might be some corrupt files or settings. Please run System Update Readiness Tool
to scan the whole computer and share us the error in CheckUSR.log:

Description of the System Update Readiness Tool for Windows Vista and for Windows Server 2008

Meanwhile, you could perform an In-place Upgrade to repair corrupted files. In-place Upgrade is a special upgrade process to repair the system. In-place
Upgrade will not affect settings like photos, movies, documents, etc. that are saved on the computer. It won’t require activation again. Please refer to the following site:

Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread. ”

What is the kind of product key you used? Was the machine activated by KMS host? If so, you may need to install the KMS Client setup key to switch the
product back to KMS client. The KMS Client setup key for Windows Server 2008 R2 Enterprise is: 489J6-VHDMP-X63PK-3K798-CPX3Y

Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread. ”

After the DISM upgrade I switched back to my original MAK key (and activated successfully). A secondary behavior of this was that Remote Desktop was no longer functional on any machine that used the MAK Key. I then did some additional research
and found that other people had experienced the same problem using the DISM upgrade (http://social.technet.microsoft.com/Forums/en-US/winserverTS/thread/6debc586-0977-4731-b418-ca1edb34fe8b).
On a hunch I switched back to the KMS key and was then able to install SP1 (and remote desktop was reenabled). I then tried a Std/Enterprise license from a different MSDN account and it activated successfully, as well as kept Remote Desktop enabled.
I also tested switching back to my original MAK key and this worked as well. I then just switched the rest of my VM's to the new MSDN key and this was successful as well, without re-introducing the KMS key.

Best I can tell, there must be something unique to using the same key at each end of the standard -> enterprise DISM upgrade path path. I've got my environment back up and running and all at SP1 but I can fire up a test VM to test a different scenario.

I started with an MSDN MAK Key, upgraded using the Server 2008 R2 Enterprise KMS key (which did not activate), then re-used my existing MSDN MAK Key, which is valid for both standard and enterprise. This is when the problems started occurring. I
then switched to a MSDN MAK Key from a different MSDN account, which resolved all of the problems. Additionally, i can re-activate the machine with the original MAK key and remote desktop continues to work.

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